Cas no 3304-51-6 ((2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid)

(2S)-2-Amino-5-(benzyloxycarbonylamino)pentanoic acid is a protected amino acid derivative widely used in peptide synthesis and pharmaceutical research. The compound features a benzyloxycarbonyl (Cbz) protecting group on the ε-amino side chain of lysine, ensuring selective reactivity during solid-phase or solution-phase peptide coupling. Its chiral (2S) configuration maintains stereochemical integrity in synthetic applications. The Cbz group offers stability under acidic and neutral conditions while being readily cleaved via hydrogenolysis, making it suitable for orthogonal protection strategies. This derivative is particularly valuable in constructing complex peptides, where controlled deprotection is critical. High purity and consistent performance make it a reliable choice for researchers requiring precise side-chain protection in amino acid modifications.
(2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid structure
3304-51-6 structure
Product Name:(2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid
CAS No:3304-51-6
MF:C13H18N2O4
MW:266.293023586273
MDL:MFCD00037220
CID:44023
PubChem ID:7009570
Update Time:2025-10-31

(2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid Chemical and Physical Properties

Names and Identifiers

    • N'-Cbz-L-ornithine
    • N'-Benzyloxycarbonyl-L-ornithine
    • L-Orn(Z)-OH
    • (S)-2-Amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid
    • H-L-ORN(Z)-OH
    • H-Orn(Z)-OH
    • N-DELTA-CBZ-D-ORNITHINE
    • (2S,4R)-1,2-Dicarbobenzyloxy-4-hydroxypyrrolidine
    • (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)
    • (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylic acid dibenzyl ester
    • (2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate
    • (2S,4R)-N-benzyloxycarbony
    • Cbz-L-Hyp-OBn
    • Cbz-L-ornithine
    • Cbz-L-ornithine NCA
    • CTK4B9600
    • H-Dapa-OH·HCl
    • SureCN2678864
    • (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid
    • (2S)-2-amino-5-[(benzyloxycarbonyl)amino]pentanoic acid
    • MFCD00037220
    • (S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid
    • (2S)-2-amino-5-{[(benzyloxy)carbonyl]amino}pentanoic acid
    • Ndelta -(benzyloxycarbonyl)-L-ornithine
    • N5 -benzyloxycarbonyl-ornithine
    • Ornithine, N5-[(phenylmethoxy)carbonyl]-
    • J-300357
    • Ndelta-Cbz-L-ornithine
    • 26780-55-2
    • AKOS015924235
    • EN300-252682
    • Ndelta -Carbobenzyloxy-L-ornithine
    • ndelta-benzyloxycarbonyl-l-ornithine
    • AS-15974
    • SCHEMBL4986552
    • 3304-51-6
    • NS00048947
    • (2S)-2-amino-5-benzyloxycarbonylaminopentanoic acid
    • VULSXQYFUHKBAN-NSHDSACASA-N
    • N-
    • (2S)-2-amino-5-(phenylmethoxycarbonylamino)pentanoic acid
    • Q-101724
    • n-delta-benzyloxycarbonyl-l-ornithine
    • ?-Benzyloxycarbonyl-L-ornithine
    • CS-W007898
    • MDL: MFCD00037220
    • Inchi: 1S/C13H18N2O4/c14-11(12(16)17)7-4-8-15-13(18)19-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9,14H2,(H,15,18)(H,16,17)/t11-/m0/s1
    • InChI Key: VULSXQYFUHKBAN-NSHDSACASA-N
    • SMILES: O(CC1C=CC=CC=1)C(NCCC[C@@H](C(=O)O)N)=O

Computed Properties

  • Exact Mass: 266.12674
  • Monoisotopic Mass: 266.12665706g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 9
  • Complexity: 290
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1.4
  • Topological Polar Surface Area: 102?2

Experimental Properties

  • Density: 1.2340
  • Melting Point: 248-252℃
  • Boiling Point: 492.2°C at 760 mmHg
  • PSA: 101.65

(2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid Security Information

(2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid Pricemore >>

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Additional information on (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid

Introduction to (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic Acid (CAS No. 3304-51-6)

(2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid, with the CAS number 3304-51-6, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and biotechnology. This compound, characterized by its unique stereochemistry and functional groups, serves as a crucial intermediate in the synthesis of various bioactive molecules. Its structural features make it particularly valuable in the development of peptidomimetics and other therapeutic agents.

The< strong>benzyloxycarbonyl group attached to the amino acid backbone provides stability and protection during synthetic processes, making it an ideal candidate for multi-step organic transformations. This protective group is commonly employed in peptide synthesis to prevent unwanted side reactions, ensuring high yields and purity of the final product. The< strong>pentanoic acid moiety contributes to the compound's solubility and reactivity, facilitating its integration into complex molecular architectures.

In recent years, there has been a surge in research focused on peptidomimetics due to their potential to mimic the biological activity of natural peptides while exhibiting improved pharmacokinetic properties. The< strong>(2S)-configuration of this compound is particularly significant, as it ensures optimal biological activity by maintaining the correct spatial orientation of functional groups. This stereochemical specificity is crucial for compounds intended for therapeutic use, where even minor structural deviations can lead to significant changes in biological efficacy.

One of the most compelling applications of (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid is in the development of enzyme inhibitors. Enzyme inhibition is a cornerstone of modern drug design, with many therapeutic agents functioning by binding to and inhibiting specific enzymatic targets. The compound's ability to serve as a building block for peptidomimetics makes it an invaluable tool for creating inhibitors with high selectivity and potency. For instance, researchers have utilized derivatives of this compound to develop inhibitors targeting proteases, which are enzymes involved in various pathological processes, including cancer and inflammation.

The< strong>benzyloxycarbonyl group can be removed under specific conditions, allowing for further functionalization or activation of the amino group. This flexibility makes (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid a versatile intermediate that can be tailored to meet the demands of different synthetic strategies. Such adaptability is particularly important in drug discovery pipelines, where compounds often undergo multiple rounds of modification before reaching their final therapeutic form.

Recent studies have also explored the use of (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid in the development of novel antibiotics. The increasing prevalence of antibiotic-resistant bacteria has necessitated the discovery of new antimicrobial agents with unique mechanisms of action. Peptidomimetics derived from this compound have shown promise in disrupting bacterial cell wall synthesis and other vital processes, offering a potential solution to the growing threat of antibiotic resistance.

The compound's< strong>pentanoic acid backbone provides a scaffold that can be modified to enhance solubility and bioavailability, critical factors for successful drug candidates. By incorporating hydrophilic or lipophilic groups at strategic positions within the molecule, researchers can fine-tune its pharmacokinetic properties. This approach has been particularly effective in designing drugs that require oral administration or targeted delivery systems.

In conclusion, (2S)-2-amino-5-(benzyloxycarbonylamino)pentanoic acid (CAS No. 3304-51-6) is a multifaceted compound with significant potential in pharmaceutical research and development. Its unique structural features make it an excellent intermediate for synthesizing peptidomimetics and other bioactive molecules. The ongoing research into its applications in enzyme inhibition, antibiotic development, and drug delivery underscores its importance in advancing therapeutic strategies.

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